Evan Osnos
Political Journalist at the New Yorker
For 300 episodes, Willy has asked the questions. Now, the tables are turned as award-winning journalist and New Yorker staff writer Evan Osnos takes over the interviewer’s chair and puts Willy in the hot seat, answering YOUR most-asked questions.
October 14, 2026 at 12:30 PM ET
In a candid and wide-ranging conversation, Willy reflects on the lessons he’s learned from building Walker & Dunlop, the risks that paid off—and the opportunities he wishes he hadn’t missed—the habits that keep him energized and curious, and what 300 conversations with some of the world’s most fascinating leaders have taught him. He also opens up about family, personal reinvention, AI and the future of work, Burning Man, whether he’d ever enter politics, and even the book he may one day write.
After 300 episodes of getting others to open up, it’s Willy’s turn.
At a glance
The Haves and Have-Yachts
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Evan gives us a fascinating look inside the world of the ultrarich, from superyachts and extravagant lifestyles to the enormous influence wealth has on American business and politics. The Haves and Have-Yachts is filled with remarkable stories, some of which are almost too outrageous to believe. Evan is a terrific storyteller, and he does a great job of making you laugh while also making you think about the growing concentration of wealth and power in America. A really fun, insightful read.
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